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Three acylated saponins and a related compound from Pithecellobium dulce.
J Nat Prod. 1997 Dec; 60(12):1269-74.JN

Abstract

Four new oleanane-type triterpene glycosides, pithedulosides H-K (1-4), were isolated from the seeds of Pithecellobium dulce. Their structures were established by extensive NMR experiments and chemical methods. Compounds 1-3 comprised acacic acid as the aglycon and either monoterpene carboxylic acid and its xyloside or monoterpene carboxylic acid as the acyl moiety at C-21. The oligosaccharide moieties linked to C-3 and C-28 were determined as alpha-L-arabinopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1 -->6)- [beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosyl and alpha-L-arabinofuranosyl-(1-->4)-[beta-D-glucopyranosyl-(1-->3)]-alpha- rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester, respectively. Compound 4 was established as an echinocystic acid 3-O-glycoside having the same sugar sequences as 1-3. Also obtained in this investigation was the known compound 5, which was identified as echinocystic acid 3-O-beta-D-xylopyranosyl- (1-->2)-alpha-L-arabinopyranosyl-(1-->6)-[beta-D-glucopyranosyl-(1 -->2)]- beta-D-glucopyranoside.

Authors+Show Affiliations

Yoshikawa K
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
Suzaki Y
No affiliation info available
Tanaka M
No affiliation info available
Arihara S
No affiliation info available
Nigam SK
No affiliation info available

MeSH

Carbohydrate SequenceHydrolysisIndiaMagnetic Resonance SpectroscopyMolecular Sequence DataPlants, MedicinalSaponinsSeedsSpectrometry, Mass, Fast Atom BombardmentTriterpenes

Pub Type(s)

Journal Article

Language

eng

PubMed ID

9428160

Citation

Yoshikawa, K, et al. "Three Acylated Saponins and a Related Compound From Pithecellobium Dulce." Journal of Natural Products, vol. 60, no. 12, 1997, pp. 1269-74.
Yoshikawa K, Suzaki Y, Tanaka M, et al. Three acylated saponins and a related compound from Pithecellobium dulce. J Nat Prod. 1997;60(12):1269-74.
Yoshikawa, K., Suzaki, Y., Tanaka, M., Arihara, S., & Nigam, S. K. (1997). Three acylated saponins and a related compound from Pithecellobium dulce. Journal of Natural Products, 60(12), 1269-74.
Yoshikawa K, et al. Three Acylated Saponins and a Related Compound From Pithecellobium Dulce. J Nat Prod. 1997;60(12):1269-74. PubMed PMID: 9428160.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Three acylated saponins and a related compound from Pithecellobium dulce. AU - Yoshikawa,K, AU - Suzaki,Y, AU - Tanaka,M, AU - Arihara,S, AU - Nigam,S K, PY - 1998/1/15/pubmed PY - 1998/1/15/medline PY - 1998/1/15/entrez SP - 1269 EP - 74 JF - Journal of natural products JO - J Nat Prod VL - 60 IS - 12 N2 - Four new oleanane-type triterpene glycosides, pithedulosides H-K (1-4), were isolated from the seeds of Pithecellobium dulce. Their structures were established by extensive NMR experiments and chemical methods. Compounds 1-3 comprised acacic acid as the aglycon and either monoterpene carboxylic acid and its xyloside or monoterpene carboxylic acid as the acyl moiety at C-21. The oligosaccharide moieties linked to C-3 and C-28 were determined as alpha-L-arabinopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1 -->6)- [beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosyl and alpha-L-arabinofuranosyl-(1-->4)-[beta-D-glucopyranosyl-(1-->3)]-alpha- rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester, respectively. Compound 4 was established as an echinocystic acid 3-O-glycoside having the same sugar sequences as 1-3. Also obtained in this investigation was the known compound 5, which was identified as echinocystic acid 3-O-beta-D-xylopyranosyl- (1-->2)-alpha-L-arabinopyranosyl-(1-->6)-[beta-D-glucopyranosyl-(1 -->2)]- beta-D-glucopyranoside. SN - 0163-3864 UR - https://www.unboundmedicine.com/medline/citation/9428160/Three_acylated_saponins_and_a_related_compound_from_Pithecellobium_dulce_ L2 - https://doi.org/10.1021/np9703555 DB - PRIME DP - Unbound Medicine ER -